diff --git a/packages/app/src/types/stream.test.ts b/packages/app/src/types/stream.test.ts
index 019f08302..653194039 100644
--- a/packages/app/src/types/stream.test.ts
+++ b/packages/app/src/types/stream.test.ts
@@ -99,6 +99,21 @@ function todoTimeline(items: { text: string; completed: boolean }[]): AgentStrea
   };
 }
 
+function compactionTimeline(
+  status: "loading" | "completed",
+  trigger?: "auto" | "manual",
+): AgentStreamEventPayload {
+  return {
+    type: "timeline",
+    provider: "pi",
+    item: {
+      type: "compaction",
+      status,
+      ...(trigger ? { trigger } : {}),
+    },
+  };
+}
+
 function findToolByCallId(state: StreamItem[], callId: string): AgentToolCallItem | undefined {
   return state.find(
     (item): item is AgentToolCallItem =>
@@ -693,6 +708,27 @@ describe("stream reducer canonical tool calls", () => {
     assert.strictEqual(todos.items[1]?.completed, true);
   });
 
+  it("preserves compaction trigger when completed update replaces loading marker", () => {
+    const state = hydrateStreamState([
+      {
+        event: compactionTimeline("loading", "auto"),
+        timestamp: new Date("2025-01-01T10:50:00Z"),
+      },
+      {
+        event: compactionTimeline("completed"),
+        timestamp: new Date("2025-01-01T10:50:01Z"),
+      },
+    ]);
+
+    const compactions = state.filter(
+      (item): item is Extract<StreamItem, { kind: "compaction" }> => item.kind === "compaction",
+    );
+
+    assert.strictEqual(compactions.length, 1);
+    assert.strictEqual(compactions[0].status, "completed");
+    assert.strictEqual(compactions[0].trigger, "auto");
+  });
+
   it("renders Claude TodoWrite as todo_list and suppresses tool call badge", () => {
     const state = hydrateStreamState([
       {
diff --git a/packages/app/src/types/stream.ts b/packages/app/src/types/stream.ts
index 44bfa2e35..c67e0d0ed 100644
--- a/packages/app/src/types/stream.ts
+++ b/packages/app/src/types/stream.ts
@@ -726,8 +726,8 @@ function reduceTimelineCompaction(
       const updated: CompactionItem = {
         ...existing,
         status: "completed",
-        trigger: item.trigger,
-        preTokens: item.preTokens,
+        trigger: item.trigger ?? existing.trigger,
+        preTokens: item.preTokens ?? existing.preTokens,
       };
       return [...state.slice(0, loadingIdx), updated, ...state.slice(loadingIdx + 1)];
     }
diff --git a/packages/server/src/server/agent/providers/codex-app-server-agent.test.ts b/packages/server/src/server/agent/providers/codex-app-server-agent.test.ts
index 6f2b84006..51d6a6825 100644
--- a/packages/server/src/server/agent/providers/codex-app-server-agent.test.ts
+++ b/packages/server/src/server/agent/providers/codex-app-server-agent.test.ts
@@ -534,6 +534,37 @@ describe("Codex app-server provider", () => {
     await session.close();
   });
 
+  test("initializes Codex app-server without making Paseo the request originator", async () => {
+    let initializeParams: unknown;
+    const appServer = createFakeCodexAppServer({
+      initialize: (params) => {
+        initializeParams = params;
+        return {};
+      },
+      "collaborationMode/list": () => ({ data: [] }),
+      "skills/list": () => ({ data: [] }),
+    });
+    const session = new CodexAppServerAgentSession(
+      createConfig({ cwd: "/workspace/project" }),
+      null,
+      createTestLogger(),
+      async () => appServer.child,
+    );
+
+    await session.connect();
+
+    expect(initializeParams).toEqual({
+      clientInfo: {
+        name: "codex_app_server_daemon",
+        title: "Codex App Server Daemon",
+        version: "0.0.0",
+      },
+      capabilities: { experimentalApi: true },
+    });
+    appServer.assertNoErrors();
+    await session.close();
+  });
+
   test("rewinds the conversation to a freshly emitted Codex user message id", async () => {
     const appServer = createFakeCodexAppServer();
     const session = new CodexAppServerAgentSession(
@@ -2703,7 +2734,17 @@ describe("Codex persisted sessions", () => {
       }),
     );
     expect(calls).toEqual([
-      { method: "initialize", params: expect.any(Object) },
+      {
+        method: "initialize",
+        params: {
+          clientInfo: {
+            name: "codex_app_server_daemon",
+            title: "Codex App Server Daemon",
+            version: "0.0.0",
+          },
+          capabilities: { experimentalApi: true },
+        },
+      },
       { method: "thread/list", params: { limit: 50, cwd: "/workspace/project-a" } },
     ]);
   });
diff --git a/packages/server/src/server/agent/providers/codex-app-server-agent.ts b/packages/server/src/server/agent/providers/codex-app-server-agent.ts
index d00fd6411..9f1dc6aa4 100644
--- a/packages/server/src/server/agent/providers/codex-app-server-agent.ts
+++ b/packages/server/src/server/agent/providers/codex-app-server-agent.ts
@@ -103,6 +103,14 @@ const TURN_START_TIMEOUT_MS = 90 * 1000;
 const INTERRUPT_TIMEOUT_MS = 2_000;
 const CODEX_PROVIDER = "codex" as const;
 const CODEX_IMAGE_ATTACHMENT_DIR = "paseo-attachments";
+// Codex treats most app-server client names as the model-request originator.
+// This reserved Codex name is non-originating, so requests keep Codex's default
+// CLI identity instead of showing up as Paseo in provider usage logs.
+const CODEX_NON_ORIGINATING_APP_SERVER_CLIENT_INFO = {
+  name: "codex_app_server_daemon",
+  title: "Codex App Server Daemon",
+  version: "0.0.0",
+} as const;
 const ASSISTANT_MESSAGE_BOUNDARY_MARKDOWN = "\n\n---\n\n";
 const CODEX_TOOL_THREAD_ITEM_TYPES = new Set([
   "commandExecution",
@@ -2818,11 +2826,7 @@ function buildCodexAppServerInitializeParams(): {
   capabilities: { experimentalApi: true };
 } {
   return {
-    clientInfo: {
-      name: "paseo",
-      title: "Paseo",
-      version: "0.0.0",
-    },
+    clientInfo: CODEX_NON_ORIGINATING_APP_SERVER_CLIENT_INFO,
     capabilities: {
       experimentalApi: true,
     },
diff --git a/packages/server/src/server/agent/providers/pi/agent.test.ts b/packages/server/src/server/agent/providers/pi/agent.test.ts
index 5b4eb5838..6866df671 100644
--- a/packages/server/src/server/agent/providers/pi/agent.test.ts
+++ b/packages/server/src/server/agent/providers/pi/agent.test.ts
@@ -2,7 +2,7 @@ import { closeSync, existsSync, fstatSync, openSync, readSync } from "node:fs";
 import pino from "pino";
 import { describe, expect, test } from "vitest";
 
-import type { AgentSessionConfig, AgentStreamEvent } from "../../agent-sdk-types.js";
+import type { AgentSession, AgentSessionConfig, AgentStreamEvent } from "../../agent-sdk-types.js";
 import { PiRpcAgentClient, PiRpcAgentSession, transformPiModels } from "./agent.js";
 import { FakePi } from "./test-utils/fake-pi.js";
 
@@ -693,12 +693,202 @@ describe("PiRpcAgentClient", () => {
     ];
 
     await expect(session.listCommands()).resolves.toEqual([
+      {
+        name: "compact",
+        description: "Manually compact the session context",
+        argumentHint: "[instructions]",
+      },
+      {
+        name: "autocompact",
+        description: "Toggle automatic context compaction",
+        argumentHint: "[on|off|toggle]",
+      },
       { name: "review", description: "Review changes", argumentHint: "" },
       { name: "fix-tests", description: "Fix tests", argumentHint: "" },
       { name: "skill:docs", description: "Read docs", argumentHint: "" },
     ]);
   });
 
+  test("lists Pi compact even when RPC get_commands omits built-in slash commands", async () => {
+    const { pi, session } = await createSession();
+    pi.latestSession().commands = [
+      { name: "review", description: "Review changes", source: "extension" },
+    ];
+
+    await expect(session.listCommands()).resolves.toContainEqual({
+      name: "compact",
+      description: "Manually compact the session context",
+      argumentHint: "[instructions]",
+    });
+    await expect(session.listCommands()).resolves.toContainEqual({
+      name: "autocompact",
+      description: "Toggle automatic context compaction",
+      argumentHint: "[on|off|toggle]",
+    });
+  });
+
+  test("preserves known argument hints when RPC get_commands returns built-in slash commands", async () => {
+    const { pi, session } = await createSession();
+    pi.latestSession().commands = [
+      { name: "compact", description: "Compact from RPC", source: "extension" },
+      { name: "autocompact", description: "Auto compact from RPC", source: "extension" },
+    ];
+
+    await expect(session.listCommands()).resolves.toEqual([
+      {
+        name: "compact",
+        description: "Compact from RPC",
+        argumentHint: "[instructions]",
+      },
+      {
+        name: "autocompact",
+        description: "Auto compact from RPC",
+        argumentHint: "[on|off|toggle]",
+      },
+    ]);
+  });
+
+  test("executes Pi compact through RPC instead of prompt text", async () => {
+    const { pi, session } = await createSession();
+    const fakeSession = pi.latestSession();
+    const handler = (session as AgentSession).tryHandleOutOfBand?.("/compact focus on tests");
+    const events: AgentStreamEvent[] = [];
+
+    expect(handler).not.toBeNull();
+    await handler?.run({ emit: (event) => events.push(event) });
+
+    expect(fakeSession.compactRequests).toEqual([{ customInstructions: "focus on tests" }]);
+    expect(fakeSession.prompts).toEqual([]);
+    expect(events).toEqual([
+      {
+        type: "timeline",
+        provider: "pi",
+        item: { type: "compaction", status: "loading", trigger: "manual" },
+      },
+      {
+        type: "timeline",
+        provider: "pi",
+        item: { type: "compaction", status: "completed", trigger: "manual" },
+      },
+    ]);
+  });
+
+  test("closes Pi compact loading marker when RPC rejects after compaction starts", async () => {
+    const { pi, session } = await createSession();
+    const fakeSession = pi.latestSession();
+    fakeSession.emitCompactEnd = false;
+    fakeSession.compactError = new Error("summarizer failed");
+    const handler = (session as AgentSession).tryHandleOutOfBand?.("/compact");
+    const events: AgentStreamEvent[] = [];
+
+    expect(handler).not.toBeNull();
+    await handler?.run({ emit: (event) => events.push(event) });
+
+    expect(events).toEqual([
+      {
+        type: "timeline",
+        provider: "pi",
+        item: { type: "compaction", status: "loading", trigger: "manual" },
+      },
+      {
+        type: "timeline",
+        provider: "pi",
+        item: { type: "compaction", status: "completed", trigger: "manual" },
+      },
+      {
+        type: "timeline",
+        provider: "pi",
+        item: {
+          type: "assistant_message",
+          text: "[Error] Failed to compact context: summarizer failed",
+        },
+      },
+    ]);
+  });
+
+  test("executes Pi autocompact through RPC instead of prompt text", async () => {
+    const { pi, session } = await createSession();
+    const fakeSession = pi.latestSession();
+    const handler = (session as AgentSession).tryHandleOutOfBand?.("/autocompact off");
+    const events: AgentStreamEvent[] = [];
+
+    expect(handler).not.toBeNull();
+    await handler?.run({ emit: (event) => events.push(event) });
+
+    expect(fakeSession.setAutoCompactionRequests).toEqual([false]);
+    expect(fakeSession.prompts).toEqual([]);
+    expect(events).toEqual([
+      {
+        type: "timeline",
+        provider: "pi",
+        item: { type: "assistant_message", text: "Auto-compaction disabled." },
+      },
+    ]);
+  });
+
+  test("rejects unknown Pi autocompact mode instead of toggling", async () => {
+    const { pi, session } = await createSession();
+    const fakeSession = pi.latestSession();
+    const handler = (session as AgentSession).tryHandleOutOfBand?.("/autocompact banana");
+    const events: AgentStreamEvent[] = [];
+
+    expect(handler).not.toBeNull();
+    await handler?.run({ emit: (event) => events.push(event) });
+
+    expect(fakeSession.setAutoCompactionRequests).toEqual([]);
+    expect(events).toEqual([
+      {
+        type: "timeline",
+        provider: "pi",
+        item: {
+          type: "assistant_message",
+          text: "[Error] Usage: /autocompact [on|off|toggle]",
+        },
+      },
+    ]);
+  });
+
+  test("toggles Pi autocompact through current RPC state", async () => {
+    const { pi, session } = await createSession();
+    const fakeSession = pi.latestSession();
+    fakeSession.state.autoCompactionEnabled = false;
+    const handler = (session as AgentSession).tryHandleOutOfBand?.("/autocompact");
+    const events: AgentStreamEvent[] = [];
+
+    expect(handler).not.toBeNull();
+    await handler?.run({ emit: (event) => events.push(event) });
+
+    expect(fakeSession.setAutoCompactionRequests).toEqual([true]);
+    expect(events).toContainEqual({
+      type: "timeline",
+      provider: "pi",
+      item: { type: "assistant_message", text: "Auto-compaction enabled." },
+    });
+  });
+
+  test("rejects Pi autocompact toggle when current RPC state is unavailable", async () => {
+    const { pi, session } = await createSession();
+    const fakeSession = pi.latestSession();
+    delete fakeSession.state.autoCompactionEnabled;
+    const handler = (session as AgentSession).tryHandleOutOfBand?.("/autocompact");
+    const events: AgentStreamEvent[] = [];
+
+    expect(handler).not.toBeNull();
+    await handler?.run({ emit: (event) => events.push(event) });
+
+    expect(fakeSession.setAutoCompactionRequests).toEqual([]);
+    expect(events).toEqual([
+      {
+        type: "timeline",
+        provider: "pi",
+        item: {
+          type: "assistant_message",
+          text: "[Error] Auto-compaction state is unavailable. Use /autocompact on or /autocompact off.",
+        },
+      },
+    ]);
+  });
+
   test("rewinds conversation through the Pi tree navigation bridge", async () => {
     const { pi, session, events } = await createSession();
     pi.latestSession().capturedUserEntries = [
diff --git a/packages/server/src/server/agent/providers/pi/agent.ts b/packages/server/src/server/agent/providers/pi/agent.ts
index b76ab5c7b..e07176a33 100644
--- a/packages/server/src/server/agent/providers/pi/agent.ts
+++ b/packages/server/src/server/agent/providers/pi/agent.ts
@@ -86,6 +86,19 @@ const QUESTION_COMMENT_HEADER = "Comment";
 const PI_ASK_USER_FREEFORM_SENTINEL = "✏️ Type custom response...";
 const COMBINED_ASK_USER_METADATA = "ask_user_select_optional_comment";
 
+const PI_HANDLED_BUILTIN_SLASH_COMMANDS: AgentSlashCommand[] = [
+  {
+    name: "compact",
+    description: "Manually compact the session context",
+    argumentHint: "[instructions]",
+  },
+  {
+    name: "autocompact",
+    description: "Toggle automatic context compaction",
+    argumentHint: "[on|off|toggle]",
+  },
+];
+
 const PI_CAPABILITIES: AgentCapabilityFlags = {
   supportsStreaming: true,
   supportsSessionPersistence: true,
@@ -205,6 +218,13 @@ interface ExtensionUiMappingOptions {
   allowFreeform?: boolean;
 }
 
+interface PiSlashCommandInvocation {
+  commandName: string;
+  args?: string;
+}
+
+type AutoCompactMode = boolean | "toggle" | "unknown";
+
 function normalizePiModelLabel(label: string): string {
   return label.trim().replace(/[_\s]+/g, " ");
 }
@@ -247,6 +267,20 @@ function normalizePiThinkingOption(value: string | null | undefined): PiThinking
   return isPiThinkingLevel(value) ? value : null;
 }
 
+function parseAutoCompactMode(value: string | undefined): AutoCompactMode {
+  const mode = (value ?? "toggle").trim().toLowerCase();
+  if (mode === "on" || mode === "true" || mode === "enable" || mode === "enabled") {
+    return true;
+  }
+  if (mode === "off" || mode === "false" || mode === "disable" || mode === "disabled") {
+    return false;
+  }
+  if (mode === "toggle") {
+    return "toggle";
+  }
+  return "unknown";
+}
+
 function mapThinkingOption(option: (typeof PI_THINKING_OPTIONS)[number]) {
   const mappedOption = {
     id: option.id,
@@ -922,6 +956,9 @@ export class PiRpcAgentSession implements AgentSession {
   private readonly seenUserEntryIds = new Set<string>();
   private readonly pendingUserMessages: PendingPiUserMessage[] = [];
   private readonly pendingExtensionResults = new Map<string, PendingExtensionResult>();
+  private outOfBandCompactionEmit: ((event: AgentStreamEvent) => void) | null = null;
+  private outOfBandCompactionStarted = false;
+  private outOfBandCompactionCompleted = false;
   private state: PiSessionState;
   private closed = false;
 
@@ -1127,11 +1164,46 @@ export class PiRpcAgentSession implements AgentSession {
 
   async listCommands(): Promise<AgentSlashCommand[]> {
     const commands = await this.runtimeSession.getCommands();
-    return commands.map((command) => ({
-      name: command.name,
-      description: command.description ?? command.source,
-      argumentHint: "",
-    }));
+    const mappedCommands = new Map<string, AgentSlashCommand>(
+      PI_HANDLED_BUILTIN_SLASH_COMMANDS.map((command) => [command.name, { ...command }]),
+    );
+    for (const command of commands) {
+      const knownCommand = mappedCommands.get(command.name);
+      mappedCommands.set(command.name, {
+        name: command.name,
+        description: command.description ?? command.source,
+        argumentHint: knownCommand?.argumentHint ?? "",
+      });
+    }
+    return [...mappedCommands.values()];
+  }
+
+  tryHandleOutOfBand(
+    prompt: AgentPromptInput,
+  ): { run(ctx: { emit: (event: AgentStreamEvent) => void }): Promise<void> } | null {
+    if (typeof prompt !== "string") {
+      return null;
+    }
+    const parsed = this.parseSlashCommandInput(prompt);
+    if (!parsed) {
+      return null;
+    }
+    const commandName = parsed.commandName.toLowerCase();
+    if (commandName === "compact") {
+      return {
+        run: async ({ emit }) => {
+          await this.executeCompactCommand(parsed.args, emit);
+        },
+      };
+    }
+    if (commandName === "autocompact") {
+      return {
+        run: async ({ emit }) => {
+          await this.executeAutoCompactCommand(parsed.args, emit);
+        },
+      };
+    }
+    return null;
   }
 
   async setModel(modelId: string | null): Promise<void> {
@@ -1172,6 +1244,128 @@ export class PiRpcAgentSession implements AgentSession {
     return this.activeTurnId ?? undefined;
   }
 
+  private parseSlashCommandInput(text: string): PiSlashCommandInvocation | null {
+    const trimmed = text.trim();
+    if (!trimmed.startsWith("/") || trimmed.length <= 1) {
+      return null;
+    }
+    const withoutPrefix = trimmed.slice(1);
+    const firstWhitespaceIdx = withoutPrefix.search(/\s/);
+    const commandName =
+      firstWhitespaceIdx === -1 ? withoutPrefix : withoutPrefix.slice(0, firstWhitespaceIdx);
+    if (!commandName || commandName.includes("/")) {
+      return null;
+    }
+    const rawArgs =
+      firstWhitespaceIdx === -1 ? "" : withoutPrefix.slice(firstWhitespaceIdx + 1).trim();
+    return rawArgs.length > 0 ? { commandName, args: rawArgs } : { commandName };
+  }
+
+  private async executeCompactCommand(
+    customInstructions: string | undefined,
+    emit: (event: AgentStreamEvent) => void,
+  ): Promise<void> {
+    if (this.outOfBandCompactionEmit) {
+      throw new Error("A Pi compact command is already running");
+    }
+    this.outOfBandCompactionEmit = emit;
+    this.outOfBandCompactionStarted = false;
+    this.outOfBandCompactionCompleted = false;
+    try {
+      await this.runtimeSession.compact(customInstructions);
+    } catch (error) {
+      const message = error instanceof Error ? error.message : String(error);
+      if (
+        this.outOfBandCompactionEmit === emit &&
+        this.outOfBandCompactionStarted &&
+        !this.outOfBandCompactionCompleted
+      ) {
+        this.emitCompactionTimeline({
+          turnId: undefined,
+          item: {
+            type: "compaction",
+            status: "completed",
+            trigger: "manual",
+          },
+        });
+      }
+      emit({
+        type: "timeline",
+        provider: PI_PROVIDER,
+        item: {
+          type: "assistant_message",
+          text: `[Error] Failed to compact context: ${message}`,
+        },
+      });
+    } finally {
+      if (this.outOfBandCompactionEmit === emit && !this.outOfBandCompactionStarted) {
+        this.outOfBandCompactionEmit = null;
+        this.outOfBandCompactionStarted = false;
+        this.outOfBandCompactionCompleted = false;
+      }
+    }
+  }
+
+  private async executeAutoCompactCommand(
+    mode: string | undefined,
+    emit: (event: AgentStreamEvent) => void,
+  ): Promise<void> {
+    let enabled = parseAutoCompactMode(mode);
+    if (enabled === "unknown") {
+      emit({
+        type: "timeline",
+        provider: PI_PROVIDER,
+        item: {
+          type: "assistant_message",
+          text: "[Error] Usage: /autocompact [on|off|toggle]",
+        },
+      });
+      return;
+    }
+    if (enabled === "toggle") {
+      const state = await this.runtimeSession.getState();
+      if (typeof state.autoCompactionEnabled !== "boolean") {
+        emit({
+          type: "timeline",
+          provider: PI_PROVIDER,
+          item: {
+            type: "assistant_message",
+            text: "[Error] Auto-compaction state is unavailable. Use /autocompact on or /autocompact off.",
+          },
+        });
+        return;
+      }
+      enabled = !state.autoCompactionEnabled;
+    }
+
+    try {
+      await this.runtimeSession.setAutoCompaction(enabled);
+    } catch (error) {
+      const message = error instanceof Error ? error.message : String(error);
+      emit({
+        type: "timeline",
+        provider: PI_PROVIDER,
+        item: {
+          type: "assistant_message",
+          text: `[Error] Failed to set auto-compaction: ${message}`,
+        },
+      });
+      return;
+    }
+    this.state = {
+      ...this.state,
+      autoCompactionEnabled: enabled,
+    };
+    emit({
+      type: "timeline",
+      provider: PI_PROVIDER,
+      item: {
+        type: "assistant_message",
+        text: `Auto-compaction ${enabled ? "enabled" : "disabled"}.`,
+      },
+    });
+  }
+
   private async requestEntryCapture(reason: string): Promise<void> {
     const requestId = randomUUID();
     const resultPromise = this.waitForExtensionResult(requestId);
@@ -1433,9 +1627,7 @@ export class PiRpcAgentSession implements AgentSession {
         return;
       }
       case "compaction_start":
-        this.emit({
-          type: "timeline",
-          provider: PI_PROVIDER,
+        this.emitCompactionTimeline({
           turnId,
           item: {
             type: "compaction",
@@ -1445,13 +1637,12 @@ export class PiRpcAgentSession implements AgentSession {
         });
         return;
       case "compaction_end":
-        this.emit({
-          type: "timeline",
-          provider: PI_PROVIDER,
+        this.emitCompactionTimeline({
           turnId,
           item: {
             type: "compaction",
             status: "completed",
+            trigger: event.reason === "manual" ? "manual" : "auto",
           },
         });
         return;
@@ -1463,6 +1654,37 @@ export class PiRpcAgentSession implements AgentSession {
     }
   }
 
+  private emitCompactionTimeline(input: {
+    turnId: string | undefined;
+    item: Extract<AgentStreamEvent, { type: "timeline" }>["item"];
+  }): void {
+    const emitOutOfBand = this.outOfBandCompactionEmit;
+    if (emitOutOfBand && input.item.type === "compaction") {
+      if (input.item.status === "loading") {
+        this.outOfBandCompactionStarted = true;
+      }
+      if (input.item.status === "completed") {
+        this.outOfBandCompactionCompleted = true;
+      }
+    }
+    const event: AgentStreamEvent = {
+      type: "timeline",
+      provider: PI_PROVIDER,
+      ...(emitOutOfBand ? {} : { turnId: input.turnId }),
+      item: input.item,
+    };
+    if (emitOutOfBand) {
+      emitOutOfBand(event);
+      if (input.item.type === "compaction" && input.item.status === "completed") {
+        this.outOfBandCompactionEmit = null;
+        this.outOfBandCompactionStarted = false;
+        this.outOfBandCompactionCompleted = false;
+      }
+      return;
+    }
+    this.emit(event);
+  }
+
   private handleMessageUpdate(
     event: Extract<PiAgentSessionEvent, { type: "message_update" }>,
     turnId: string | undefined,
diff --git a/packages/server/src/server/agent/providers/pi/cli-runtime.ts b/packages/server/src/server/agent/providers/pi/cli-runtime.ts
index 84f8cbaf9..07af803a0 100644
--- a/packages/server/src/server/agent/providers/pi/cli-runtime.ts
+++ b/packages/server/src/server/agent/providers/pi/cli-runtime.ts
@@ -129,6 +129,17 @@ class PiCliRuntimeSession implements PiRuntimeSession {
     await this.request({ type: "prompt", message, ...(images?.length ? { images } : {}) });
   }
 
+  async compact(customInstructions?: string): Promise<void> {
+    await this.request({
+      type: "compact",
+      ...(customInstructions ? { customInstructions } : {}),
+    });
+  }
+
+  async setAutoCompaction(enabled: boolean): Promise<void> {
+    await this.request({ type: "set_auto_compaction", enabled });
+  }
+
   async abort(): Promise<void> {
     await this.request({ type: "abort" });
   }
diff --git a/packages/server/src/server/agent/providers/pi/rpc-types.ts b/packages/server/src/server/agent/providers/pi/rpc-types.ts
index 90f9aa4e1..b25a61659 100644
--- a/packages/server/src/server/agent/providers/pi/rpc-types.ts
+++ b/packages/server/src/server/agent/providers/pi/rpc-types.ts
@@ -79,6 +79,7 @@ export interface PiSessionState {
   thinkingLevel: PiThinkingLevel;
   isStreaming: boolean;
   isCompacting: boolean;
+  autoCompactionEnabled?: boolean;
   sessionFile?: string;
   sessionId: string;
   sessionName?: string;
@@ -111,6 +112,8 @@ export interface PiRpcSlashCommand {
 
 export type PiRpcCommand =
   | { id?: string; type: "prompt"; message: string; images?: PiImageContent[] }
+  | { id?: string; type: "compact"; customInstructions?: string }
+  | { id?: string; type: "set_auto_compaction"; enabled: boolean }
   | { id?: string; type: "abort" }
   | { id?: string; type: "get_state" }
   | { id?: string; type: "get_messages" }
diff --git a/packages/server/src/server/agent/providers/pi/runtime.ts b/packages/server/src/server/agent/providers/pi/runtime.ts
index e479c5894..0d813c12f 100644
--- a/packages/server/src/server/agent/providers/pi/runtime.ts
+++ b/packages/server/src/server/agent/providers/pi/runtime.ts
@@ -37,6 +37,8 @@ export interface PiRuntimeSession {
     message: string,
     images?: Array<{ type: "image"; data: string; mimeType: string }>,
   ): Promise<void>;
+  compact(customInstructions?: string): Promise<void>;
+  setAutoCompaction(enabled: boolean): Promise<void>;
   abort(): Promise<void>;
   getState(): Promise<PiSessionState>;
   getMessages(): Promise<PiAgentMessage[]>;
diff --git a/packages/server/src/server/agent/providers/pi/test-utils/fake-pi.ts b/packages/server/src/server/agent/providers/pi/test-utils/fake-pi.ts
index 08d92f201..53121c23a 100644
--- a/packages/server/src/server/agent/providers/pi/test-utils/fake-pi.ts
+++ b/packages/server/src/server/agent/providers/pi/test-utils/fake-pi.ts
@@ -51,6 +51,8 @@ export class FakePi implements PiRuntime {
 
 export class FakePiSession implements PiRuntimeSession {
   readonly prompts: Array<{ message: string; imageCount: number }> = [];
+  readonly compactRequests: Array<{ customInstructions?: string }> = [];
+  readonly setAutoCompactionRequests: boolean[] = [];
   readonly setModelRequests: Array<{ provider: string; modelId: string }> = [];
   readonly setThinkingLevelRequests: string[] = [];
   readonly treeNavigationRequests: string[] = [];
@@ -69,6 +71,8 @@ export class FakePiSession implements PiRuntimeSession {
     cost: 0,
   };
   commands: PiRpcSlashCommand[] = [];
+  compactError: Error | null = null;
+  emitCompactEnd = true;
   state: PiSessionState;
 
   private readonly subscribers = new Set<(event: PiRuntimeEvent) => void>();
@@ -79,6 +83,7 @@ export class FakePiSession implements PiRuntimeSession {
       thinkingLevel: "medium",
       isStreaming: false,
       isCompacting: false,
+      autoCompactionEnabled: true,
       sessionFile: launch.session ?? "/tmp/pi-session",
       sessionId: "pi-session-1",
       messageCount: 0,
@@ -102,6 +107,25 @@ export class FakePiSession implements PiRuntimeSession {
     this.handleEntryCaptureCommand(message);
   }
 
+  async compact(customInstructions?: string): Promise<void> {
+    this.compactRequests.push(customInstructions === undefined ? {} : { customInstructions });
+    this.emit({ type: "compaction_start", reason: "manual" });
+    if (this.emitCompactEnd) {
+      this.emit({ type: "compaction_end", reason: "manual" });
+    }
+    if (this.compactError) {
+      throw this.compactError;
+    }
+  }
+
+  async setAutoCompaction(enabled: boolean): Promise<void> {
+    this.setAutoCompactionRequests.push(enabled);
+    this.state = {
+      ...this.state,
+      autoCompactionEnabled: enabled,
+    };
+  }
+
   async abort(): Promise<void> {
     this.abortRequested = true;
   }
diff --git a/packages/server/src/server/auto-archive-on-merge/archive-if-safe.test.ts b/packages/server/src/server/auto-archive-on-merge/archive-if-safe.test.ts
index 789326195..6531cde4a 100644
--- a/packages/server/src/server/auto-archive-on-merge/archive-if-safe.test.ts
+++ b/packages/server/src/server/auto-archive-on-merge/archive-if-safe.test.ts
@@ -233,15 +233,15 @@ describe("archiveIfSafe", () => {
     expect(harness.deps.archivePaseoWorktree).not.toHaveBeenCalled();
   });
 
-  test("does nothing when the upstream status is unknown", async () => {
+  test("archives when the PR is merged and the upstream branch was deleted", async () => {
     const harness = createHarness({
-      getSnapshot: async () => createSnapshot({ git: { aheadOfOrigin: null } }),
+      getSnapshot: async () =>
+        createSnapshot({ git: { aheadOfOrigin: null, behindOfOrigin: null } }),
     });
 
     await runArchiveIfSafe(harness);
 
-    expect(harness.deps.isPaseoOwnedWorktreeCwd).not.toHaveBeenCalled();
-    expect(harness.deps.archivePaseoWorktree).not.toHaveBeenCalled();
+    expect(harness.deps.archivePaseoWorktree).toHaveBeenCalledTimes(1);
   });
 
   test("does nothing when the cwd is not a Paseo-owned worktree", async () => {
diff --git a/packages/server/src/server/auto-archive-on-merge/archive-if-safe.ts b/packages/server/src/server/auto-archive-on-merge/archive-if-safe.ts
index d98ceaa86..7831a733e 100644
--- a/packages/server/src/server/auto-archive-on-merge/archive-if-safe.ts
+++ b/packages/server/src/server/auto-archive-on-merge/archive-if-safe.ts
@@ -78,10 +78,10 @@ export async function archiveIfSafe(input: {
       return;
     }
 
-    if (snapshot.git.isDirty === true || snapshot.git.aheadOfOrigin === null) {
+    if (snapshot.git.isDirty === true) {
       return;
     }
-    if (snapshot.git.aheadOfOrigin > 0) {
+    if (typeof snapshot.git.aheadOfOrigin === "number" && snapshot.git.aheadOfOrigin > 0) {
       return;
     }
 
diff --git a/packages/server/src/server/daemon-e2e/pi.real.e2e.test.ts b/packages/server/src/server/daemon-e2e/pi.real.e2e.test.ts
index 8b2a9cd40..8140a6517 100644
--- a/packages/server/src/server/daemon-e2e/pi.real.e2e.test.ts
+++ b/packages/server/src/server/daemon-e2e/pi.real.e2e.test.ts
@@ -1,4 +1,4 @@
-import { existsSync, mkdtempSync, readFileSync, rmSync, writeFileSync } from "node:fs";
+import { existsSync, mkdirSync, mkdtempSync, readFileSync, rmSync, writeFileSync } from "node:fs";
 import { tmpdir } from "node:os";
 import path from "node:path";
 import { randomUUID } from "node:crypto";
@@ -24,6 +24,7 @@ process.env.PASEO_SUPERVISED = "0";
 
 const PI_TEST_TIMEOUT_MS = 240_000;
 const PI_REAL_TEST_MODEL = getRealProviderConfig("pi").model;
+const PI_FREE_COMPACTION_TEST_MODEL = "openrouter/openai/gpt-oss-20b:free";
 
 type ToolCallItem = Extract<AgentTimelineItem, { type: "tool_call" }>;
 
@@ -31,6 +32,18 @@ function tmpCwd(prefix = "daemon-real-pi-"): string {
   return mkdtempSync(path.join(tmpdir(), prefix));
 }
 
+function sleep(ms: number): Promise<void> {
+  return new Promise((resolve) => setTimeout(resolve, ms));
+}
+
+function writePiCompactionSettings(
+  cwd: string,
+  compaction: { enabled: boolean; reserveTokens?: number; keepRecentTokens?: number },
+): void {
+  mkdirSync(path.join(cwd, ".pi"), { recursive: true });
+  writeFileSync(path.join(cwd, ".pi/settings.json"), JSON.stringify({ compaction }, null, 2));
+}
+
 function createPiClient(): AgentClient {
   return createRealProviderClient("pi", pino({ level: "silent" }));
 }
@@ -68,6 +81,27 @@ async function fetchCanonicalTimeline(
   return timeline.entries.map((entry) => entry.item);
 }
 
+async function waitForTimelineItem(
+  client: DaemonClient,
+  agentId: string,
+  predicate: (item: AgentTimelineItem) => boolean,
+  timeoutMs = PI_TEST_TIMEOUT_MS,
+): Promise<AgentTimelineItem> {
+  const deadline = Date.now() + timeoutMs;
+  let lastItems: AgentTimelineItem[] = [];
+  while (Date.now() < deadline) {
+    lastItems = await fetchCanonicalTimeline(client, agentId);
+    const item = lastItems.find(predicate);
+    if (item) {
+      return item;
+    }
+    await sleep(250);
+  }
+  throw new Error(
+    `Timed out waiting for Pi timeline item. Last timeline: ${JSON.stringify(lastItems)}`,
+  );
+}
+
 async function withConnectedPiDaemon(
   run: (context: { client: DaemonClient }) => Promise<void>,
 ): Promise<void> {
@@ -101,6 +135,200 @@ beforeEach((context) => {
   }
 });
 
+test(
+  "real Pi daemon lists Paseo-handled compact slash commands",
+  async () => {
+    const cwd = tmpCwd("pi-compact-commands-");
+
+    try {
+      await withConnectedPiDaemon(async ({ client }) => {
+        const agent = await client.createAgent({
+          cwd,
+          title: "pi-compact-commands",
+          provider: "pi",
+          model: PI_FREE_COMPACTION_TEST_MODEL,
+        });
+
+        const result = await client.listCommands(agent.id);
+        expect(result.commands).toEqual(
+          expect.arrayContaining([
+            expect.objectContaining({
+              name: "compact",
+              description: "Manually compact the session context",
+            }),
+            expect.objectContaining({
+              name: "autocompact",
+              description: "Toggle automatic context compaction",
+            }),
+          ]),
+        );
+      });
+    } finally {
+      rmSync(cwd, { recursive: true, force: true });
+    }
+  },
+  PI_TEST_TIMEOUT_MS,
+);
+
+test(
+  "real Pi daemon executes manual compact out-of-band instead of prompt text",
+  async () => {
+    const cwd = tmpCwd("pi-manual-compact-");
+
+    try {
+      writePiCompactionSettings(cwd, {
+        enabled: true,
+        keepRecentTokens: 1,
+      });
+
+      await withConnectedPiDaemon(async ({ client }) => {
+        const agent = await client.createAgent({
+          cwd,
+          title: "pi-manual-compact",
+          provider: "pi",
+          model: PI_FREE_COMPACTION_TEST_MODEL,
+        });
+
+        await client.sendMessage(agent.id, "Reply exactly: compact-ready");
+        const finish = await client.waitForFinish(agent.id, PI_TEST_TIMEOUT_MS);
+        expect(finish.status).toBe("idle");
+
+        await client.sendMessage(agent.id, "/compact summarize this e2e run");
+
+        await waitForTimelineItem(
+          client,
+          agent.id,
+          (item) => item.type === "compaction" && item.status === "completed",
+        );
+
+        const items = await fetchCanonicalTimeline(client, agent.id);
+        expect(items).toEqual(
+          expect.arrayContaining([
+            expect.objectContaining({
+              type: "compaction",
+              status: "loading",
+              trigger: "manual",
+            }),
+            expect.objectContaining({
+              type: "compaction",
+              status: "completed",
+            }),
+          ]),
+        );
+        expect(
+          items.some((item) => item.type === "user_message" && item.text.includes("/compact")),
+        ).toBe(false);
+        expect(
+          items.some(
+            (item) => item.type === "assistant_message" && item.text.includes("Failed to compact"),
+          ),
+        ).toBe(false);
+      });
+    } finally {
+      rmSync(cwd, { recursive: true, force: true });
+    }
+  },
+  PI_TEST_TIMEOUT_MS,
+);
+
+test(
+  "real Pi daemon toggles auto-compaction out-of-band instead of prompt text",
+  async () => {
+    const cwd = tmpCwd("pi-autocompact-toggle-");
+
+    try {
+      await withConnectedPiDaemon(async ({ client }) => {
+        const agent = await client.createAgent({
+          cwd,
+          title: "pi-autocompact-toggle",
+          provider: "pi",
+          model: PI_FREE_COMPACTION_TEST_MODEL,
+        });
+
+        await client.sendMessage(agent.id, "/autocompact off");
+        await waitForTimelineItem(
+          client,
+          agent.id,
+          (item) => item.type === "assistant_message" && item.text === "Auto-compaction disabled.",
+        );
+
+        await client.sendMessage(agent.id, "/autocompact");
+        await waitForTimelineItem(
+          client,
+          agent.id,
+          (item) => item.type === "assistant_message" && item.text === "Auto-compaction enabled.",
+        );
+
+        const items = await fetchCanonicalTimeline(client, agent.id);
+        expect(
+          items.some((item) => item.type === "user_message" && item.text.includes("/autocompact")),
+        ).toBe(false);
+      });
+    } finally {
+      rmSync(cwd, { recursive: true, force: true });
+    }
+  },
+  PI_TEST_TIMEOUT_MS,
+);
+
+test(
+  "real Pi daemon surfaces automatic threshold compaction events",
+  async () => {
+    const cwd = tmpCwd("pi-auto-compact-");
+
+    try {
+      writePiCompactionSettings(cwd, {
+        enabled: true,
+        reserveTokens: 126_000,
+        keepRecentTokens: 1,
+      });
+
+      await withConnectedPiDaemon(async ({ client }) => {
+        const agent = await client.createAgent({
+          cwd,
+          title: "pi-auto-compact",
+          provider: "pi",
+          model: PI_FREE_COMPACTION_TEST_MODEL,
+        });
+
+        await client.sendMessage(agent.id, "Reply exactly: auto-compact-ready");
+        const finish = await client.waitForFinish(agent.id, PI_TEST_TIMEOUT_MS);
+        expect(finish.status, JSON.stringify(finish)).toBe("idle");
+
+        await waitForTimelineItem(
+          client,
+          agent.id,
+          (item) => item.type === "compaction" && item.status === "completed",
+        );
+
+        const items = await fetchCanonicalTimeline(client, agent.id);
+        expect(items).toEqual(
+          expect.arrayContaining([
+            expect.objectContaining({
+              type: "compaction",
+              status: "loading",
+              trigger: "auto",
+            }),
+            expect.objectContaining({
+              type: "compaction",
+              status: "completed",
+            }),
+          ]),
+        );
+        expect(
+          items.some(
+            (item) =>
+              item.type === "assistant_message" && item.text.includes("Auto-compaction failed"),
+          ),
+        ).toBe(false);
+      });
+    } finally {
+      rmSync(cwd, { recursive: true, force: true });
+    }
+  },
+  PI_TEST_TIMEOUT_MS,
+);
+
 test(
   "bash tool call records completed shell detail and output",
   async () => {
diff --git a/packages/server/src/server/speech/providers/local/runtime.ts b/packages/server/src/server/speech/providers/local/runtime.ts
index 0653a75e5..ba9ec9aac 100644
--- a/packages/server/src/server/speech/providers/local/runtime.ts
+++ b/packages/server/src/server/speech/providers/local/runtime.ts
@@ -156,6 +156,7 @@ export async function initializeLocalSpeechServices(params: {
 
   const workerClient = localConfig
     ? new LocalSpeechWorkerClient({
+        logger,
         config: {
           modelsDir: localConfig.modelsDir,
           voiceSttModel: localModels.voiceLocalSttModel,
diff --git a/packages/server/src/server/speech/providers/local/worker-client.test.ts b/packages/server/src/server/speech/providers/local/worker-client.test.ts
index b42ff4adc..3c028be13 100644
--- a/packages/server/src/server/speech/providers/local/worker-client.test.ts
+++ b/packages/server/src/server/speech/providers/local/worker-client.test.ts
@@ -20,6 +20,8 @@ import { bufferToWorkerBytes, workerBytesToBuffer } from "./worker-bytes.js";
 class FakeLocalSpeechWorker extends EventEmitter {
   public connected = true;
   public killed = false;
+  public pid = 12345;
+  public readonly stderr = new EventEmitter() as NodeJS.ReadableStream;
   public readonly sent: LocalSpeechWorkerRequest[] = [];
   public disconnects = 0;
   public kills = 0;
@@ -88,9 +90,9 @@ class PausedIpcWorker {
   }
 
   on(event: "message", listener: (message: LocalSpeechWorkerToParentMessage) => void): this;
-  on(event: "exit", listener: (code: number | null, signal: NodeJS.Signals | null) => void): this;
+  on(event: "close", listener: (code: number | null, signal: NodeJS.Signals | null) => void): this;
   on(
-    event: "message" | "exit",
+    event: "message" | "close",
     listener:
       | ((message: LocalSpeechWorkerToParentMessage) => void)
       | ((code: number | null, signal: NodeJS.Signals | null) => void),
@@ -103,6 +105,7 @@ class PausedIpcWorker {
 function createClient(options?: { idleTtlMs?: number }) {
   const workers: FakeLocalSpeechWorker[] = [];
   const client = new LocalSpeechWorkerClient({
+    logger: pino({ level: "silent" }),
     config: {
       modelsDir: "/tmp/models",
       voiceSttModel: "parakeet-tdt-0.6b-v2-int8",
@@ -120,6 +123,19 @@ function createClient(options?: { idleTtlMs?: number }) {
   return { client, workers };
 }
 
+function createCapturingLogger(): { logger: pino.Logger; records: Array<Record<string, unknown>> } {
+  const records: Array<Record<string, unknown>> = [];
+  const logger = pino(
+    { level: "trace" },
+    {
+      write(line: string) {
+        records.push(JSON.parse(line) as Record<string, unknown>);
+      },
+    },
+  );
+  return { logger, records };
+}
+
 async function waitForMicrotasks(): Promise<void> {
   await new Promise((resolve) => setTimeout(resolve, 0));
 }
@@ -217,6 +233,7 @@ describe("LocalSpeechWorkerClient", () => {
   it("does not surface real IPC backpressure when replaying native-sized dictation frames", async () => {
     const workers: PausedIpcWorker[] = [];
     const client = new LocalSpeechWorkerClient({
+      logger: pino({ level: "silent" }),
       config: {
         modelsDir: "/tmp/models",
         voiceSttModel: "parakeet-tdt-0.6b-v2-int8",
@@ -257,6 +274,80 @@ describe("LocalSpeechWorkerClient", () => {
     }
   });
 
+  it("logs worker exit details and includes actionable context in the surfaced error", async () => {
+    const { logger, records } = createCapturingLogger();
+    const workers: FakeLocalSpeechWorker[] = [];
+    const client = new LocalSpeechWorkerClient({
+      logger,
+      config: {
+        modelsDir: "/tmp/models",
+        voiceSttModel: "parakeet-tdt-0.6b-v2-int8",
+        dictationSttModel: "parakeet-tdt-0.6b-v2-int8",
+        voiceTtsModel: "kokoro-en-v0_19",
+      },
+      forkWorker: () => {
+        const worker = new FakeLocalSpeechWorker();
+        workers.push(worker);
+        return worker;
+      },
+    });
+    const provider = new WorkerBackedSpeechToTextProvider(client, "dictationStt");
+    const session = provider.createSession({ logger: pino({ level: "silent" }) });
+
+    const connect = session.connect();
+    workers[0].emit("exit", null, "SIGABRT");
+    workers[0].stderr.emit("data", "dyld: Library not loaded: libsherpa-onnx-c-api.dylib");
+    workers[0].emit("close", null, "SIGABRT");
+
+    await expect(connect).rejects.toThrow(
+      "Local speech worker exited (signal SIGABRT) while handling session.create (dictationStt). Last stderr: dyld: Library not loaded: libsherpa-onnx-c-api.dylib",
+    );
+    const exitRecord = records.find((record) => record.msg === "Local speech worker exited");
+    expect(exitRecord).toMatchObject({
+      workerPid: 12345,
+      signal: "SIGABRT",
+      stderrTail: "dyld: Library not loaded: libsherpa-onnx-c-api.dylib",
+      pendingRequests: [expect.objectContaining({ type: "session.create", kind: "dictationStt" })],
+    });
+  });
+
+  it("does not log intentional shutdowns as worker crashes", async () => {
+    const { logger, records } = createCapturingLogger();
+    const workers: FakeLocalSpeechWorker[] = [];
+    const client = new LocalSpeechWorkerClient({
+      logger,
+      config: {
+        modelsDir: "/tmp/models",
+        voiceSttModel: "parakeet-tdt-0.6b-v2-int8",
+        dictationSttModel: "parakeet-tdt-0.6b-v2-int8",
+        voiceTtsModel: "kokoro-en-v0_19",
+      },
+      forkWorker: () => {
+        const worker = new FakeLocalSpeechWorker();
+        workers.push(worker);
+        return worker;
+      },
+    });
+
+    const synthesize = client.synthesizeSpeech("hello");
+    workers[0].respond(workers[0].sent[0], {
+      audio: bufferToWorkerBytes(Buffer.from([1])),
+      format: "pcm;rate=24000",
+    });
+    await synthesize;
+
+    client.shutdown();
+    workers[0].emit("close", null, "SIGTERM");
+
+    expect(records.find((record) => record.msg === "Local speech worker exited")).toBeUndefined();
+    expect(
+      records.find((record) => record.msg === "Local speech worker closed after shutdown"),
+    ).toMatchObject({
+      workerPid: 12345,
+      signal: "SIGTERM",
+    });
+  });
+
   it("forwards VAD session events through the shared worker", async () => {
     const { client, workers } = createClient();
     const provider = new WorkerBackedTurnDetectionProvider(client);
diff --git a/packages/server/src/server/speech/providers/local/worker-client.ts b/packages/server/src/server/speech/providers/local/worker-client.ts
index 88c0d46fb..1f0fa96b9 100644
--- a/packages/server/src/server/speech/providers/local/worker-client.ts
+++ b/packages/server/src/server/speech/providers/local/worker-client.ts
@@ -28,6 +28,8 @@ import { bufferToWorkerBytes, workerBytesToBuffer } from "./worker-bytes.js";
 const DEFAULT_REQUEST_TIMEOUT_MS = 30000;
 const DEFAULT_IDLE_TTL_MS = 5 * 60 * 1000;
 const DEFAULT_LOCAL_SAMPLE_RATE = 16000;
+const STDERR_TAIL_MAX_CHARS = 8000;
+const USER_ERROR_STDERR_MAX_CHARS = 1000;
 
 type LocalSpeechWorkerRequestInput = LocalSpeechWorkerRequest extends infer Request
   ? Request extends LocalSpeechWorkerRequest
@@ -38,21 +40,27 @@ type LocalSpeechWorkerRequestInput = LocalSpeechWorkerRequest extends infer Requ
 interface LocalSpeechWorkerProcess {
   connected: boolean;
   killed: boolean;
+  pid?: number;
+  stderr?: Readable | null;
   send(message: LocalSpeechWorkerRequest, callback: (error: Error | null) => void): boolean;
   disconnect(): void;
   kill(): boolean;
   on(event: "message", listener: (message: LocalSpeechWorkerToParentMessage) => void): this;
-  on(event: "exit", listener: (code: number | null, signal: NodeJS.Signals | null) => void): this;
+  on(event: "close", listener: (code: number | null, signal: NodeJS.Signals | null) => void): this;
 }
 
 interface PendingRequest {
   resolve: (value: unknown) => void;
   reject: (error: Error) => void;
   timeout: ReturnType<typeof setTimeout>;
+  type: LocalSpeechWorkerRequest["type"];
+  summary: Record<string, unknown>;
+  startedAt: number;
 }
 
 interface LocalSpeechWorkerClientOptions {
   config: LocalSpeechWorkerConfig;
+  logger: pino.Logger;
   requestTimeoutMs?: number;
   idleTtlMs?: number;
   forkWorker?: () => LocalSpeechWorkerProcess;
@@ -90,7 +98,7 @@ function forkLocalSpeechWorker(): LocalSpeechWorkerProcess {
     env,
     execArgv: resolveWorkerExecArgv(),
     serialization: "advanced",
-    stdio: ["ignore", "ignore", "inherit", "ipc"],
+    stdio: ["ignore", "ignore", "pipe", "ipc"],
   }) as LocalSpeechWorkerProcess;
 }
 
@@ -100,8 +108,75 @@ function isResponse(
   return message.type === "response";
 }
 
+function truncateStart(value: string, maxChars: number): string {
+  if (value.length <= maxChars) {
+    return value;
+  }
+  return value.slice(value.length - maxChars);
+}
+
+function summarizeWorkerRequest(message: LocalSpeechWorkerRequest): Record<string, unknown> {
+  switch (message.type) {
+    case "session.create":
+      return { kind: message.kind, sessionId: message.sessionId };
+    case "session.append":
+      return { sessionId: message.sessionId, audioBytes: message.audio.byteLength };
+    case "session.commit":
+    case "session.clear":
+    case "session.flush":
+    case "session.reset":
+    case "session.close":
+      return { sessionId: message.sessionId };
+    case "stt.transcribe":
+      return {
+        model: message.model,
+        audioBytes: message.audio.byteLength,
+        format: message.format,
+      };
+    case "tts.synthesize":
+      return { textLength: message.text.length };
+  }
+}
+
+function formatExitStatus(code: number | null, signal: NodeJS.Signals | null): string {
+  const parts: string[] = [];
+  if (code !== null) {
+    parts.push(`code ${code}`);
+  }
+  if (signal) {
+    parts.push(`signal ${signal}`);
+  }
+  return parts.length > 0 ? parts.join(", ") : "unknown exit status";
+}
+
+function formatPendingRequestForMessage(request: Record<string, unknown>): string {
+  const type = typeof request.type === "string" ? request.type : "unknown request";
+  const kind = typeof request.kind === "string" ? ` (${request.kind})` : "";
+  return `${type}${kind}`;
+}
+
+function buildWorkerExitMessage(params: {
+  code: number | null;
+  signal: NodeJS.Signals | null;
+  pendingRequests: Array<Record<string, unknown>>;
+  stderrTail: string;
+}): string {
+  const pending =
+    params.pendingRequests.length > 0
+      ? ` while handling ${params.pendingRequests
+          .slice(0, 3)
+          .map(formatPendingRequestForMessage)
+          .join(", ")}`
+      : "";
+  const stderr = params.stderrTail
+    ? ` Last stderr: ${truncateStart(params.stderrTail, USER_ERROR_STDERR_MAX_CHARS)}`
+    : " Check daemon.log and macOS DiagnosticReports for Paseo Voice crash details.";
+  return `Local speech worker exited (${formatExitStatus(params.code, params.signal)})${pending}.${stderr}`;
+}
+
 export class LocalSpeechWorkerClient {
   private readonly config: LocalSpeechWorkerConfig;
+  private readonly logger: pino.Logger;
   private readonly requestTimeoutMs: number;
   private readonly idleTtlMs: number;
   private readonly forkWorker: () => LocalSpeechWorkerProcess;
@@ -109,11 +184,16 @@ export class LocalSpeechWorkerClient {
   private readonly activeSessionIds = new Set<string>();
   private readonly sessionEmitters = new Map<string, EventEmitter>();
   private worker: LocalSpeechWorkerProcess | null = null;
+  private workerPid: number | null = null;
+  private stderrTail = "";
+  private stderrLineBuffer = "";
   private inFlightRequests = 0;
   private idleTimer: ReturnType<typeof setTimeout> | null = null;
+  private readonly intentionalWorkerCloses = new WeakSet<LocalSpeechWorkerProcess>();
 
   constructor(options: LocalSpeechWorkerClientOptions) {
     this.config = options.config;
+    this.logger = options.logger.child({ component: "local-speech-worker-client" });
     this.requestTimeoutMs = options.requestTimeoutMs ?? DEFAULT_REQUEST_TIMEOUT_MS;
     this.idleTtlMs = options.idleTtlMs ?? DEFAULT_IDLE_TTL_MS;
     this.forkWorker = options.forkWorker ?? forkLocalSpeechWorker;
@@ -214,7 +294,9 @@ export class LocalSpeechWorkerClient {
     this.sessionEmitters.clear();
     const worker = this.worker;
     this.worker = null;
+    this.workerPid = null;
     if (worker && !worker.killed) {
+      this.intentionalWorkerCloses.add(worker);
       try {
         worker.disconnect();
       } catch {
@@ -232,6 +314,7 @@ export class LocalSpeechWorkerClient {
     const worker = this.ensureWorker();
     const requestId = randomUUID();
     const message = { ...input, requestId } as LocalSpeechWorkerRequest;
+    const requestSummary = summarizeWorkerRequest(message);
     this.inFlightRequests++;
     this.clearIdleTimer();
 
@@ -246,6 +329,9 @@ export class LocalSpeechWorkerClient {
         resolve: (value) => resolve(value as T),
         reject,
         timeout,
+        type: message.type,
+        summary: requestSummary,
+        startedAt: Date.now(),
       });
 
       worker.send(message, (error) => {
@@ -271,11 +357,44 @@ export class LocalSpeechWorkerClient {
     }
     const worker = this.forkWorker();
     this.worker = worker;
+    this.workerPid = worker.pid ?? null;
+    this.stderrTail = "";
+    this.stderrLineBuffer = "";
+    this.logger.info(
+      {
+        workerPid: this.workerPid,
+        modelsDir: this.config.modelsDir,
+        voiceSttModel: this.config.voiceSttModel,
+        dictationSttModel: this.config.dictationSttModel,
+        voiceTtsModel: this.config.voiceTtsModel,
+      },
+      "Local speech worker spawned",
+    );
+    worker.stderr?.on("data", (chunk: Buffer | string) => this.handleWorkerStderr(chunk));
     worker.on("message", (message) => this.handleWorkerMessage(message));
-    worker.on("exit", () => this.handleWorkerExit());
+    worker.on("close", (code, signal) => this.handleWorkerExit(worker, code, signal));
     return worker;
   }
 
+  private handleWorkerStderr(chunk: Buffer | string): void {
+    const text = Buffer.isBuffer(chunk) ? chunk.toString("utf8") : chunk;
+    this.stderrTail = truncateStart(this.stderrTail + text, STDERR_TAIL_MAX_CHARS);
+
+    this.stderrLineBuffer += text;
+    const lines = this.stderrLineBuffer.split(/\r?\n/);
+    this.stderrLineBuffer = lines.pop() ?? "";
+    for (const line of lines) {
+      const trimmed = line.trim();
+      if (!trimmed) {
+        continue;
+      }
+      this.logger.warn(
+        { workerPid: this.workerPid, stderr: trimmed },
+        "Local speech worker stderr",
+      );
+    }
+  }
+
   private handleWorkerMessage(message: LocalSpeechWorkerToParentMessage): void {
     if (isResponse(message)) {
       const pending = this.pendingRequests.get(message.requestId);
@@ -317,13 +436,84 @@ export class LocalSpeechWorkerClient {
     }
   }
 
-  private handleWorkerExit(): void {
-    this.worker = null;
+  private handleWorkerExit(
+    worker: LocalSpeechWorkerProcess,
+    code: number | null,
+    signal: NodeJS.Signals | null,
+  ): void {
+    const wasCurrentWorker = this.worker === worker;
+    const wasIntentionalClose = this.intentionalWorkerCloses.has(worker);
+    this.intentionalWorkerCloses.delete(worker);
+    const workerPid = worker.pid ?? (wasCurrentWorker ? this.workerPid : null);
+    const pendingRequests = this.describePendingRequests();
+    const activeSessionCount = this.activeSessionIds.size;
+    const stderrTail = this.getStderrTail();
+
+    if (wasIntentionalClose) {
+      this.logger.info(
+        {
+          workerPid,
+          code,
+          signal,
+          pendingRequests,
+          activeSessionCount,
+          stderrTail: stderrTail || null,
+        },
+        "Local speech worker closed after shutdown",
+      );
+      if (wasCurrentWorker) {
+        this.worker = null;
+        this.workerPid = null;
+      }
+      return;
+    }
+
+    if (!wasCurrentWorker) {
+      this.logger.warn(
+        {
+          workerPid,
+          code,
+          signal,
+          pendingRequests,
+          activeSessionCount,
+          stderrTail: stderrTail || null,
+        },
+        "Stale local speech worker closed",
+      );
+      return;
+    }
+
+    const error = new Error(
+      buildWorkerExitMessage({
+        code,
+        signal,
+        pendingRequests,
+        stderrTail,
+      }),
+    );
+
+    this.logger.error(
+      {
+        err: error,
+        workerPid,
+        code,
+        signal,
+        pendingRequests,
+        activeSessionCount,
+        stderrTail: stderrTail || null,
+      },
+      "Local speech worker exited",
+    );
+
+    if (wasCurrentWorker) {
+      this.worker = null;
+      this.workerPid = null;
+    }
     this.clearIdleTimer();
-    this.rejectAllPending(new Error("Local speech worker exited"));
+    this.rejectAllPending(error);
     for (const [sessionId, emitter] of this.sessionEmitters) {
       if (this.activeSessionIds.has(sessionId)) {
-        emitter.emit("error", new Error("Local speech worker exited"));
+        this.emitErrorIfObserved(sessionId, emitter, error, workerPid);
       }
     }
     this.activeSessionIds.clear();
@@ -331,6 +521,24 @@ export class LocalSpeechWorkerClient {
     this.inFlightRequests = 0;
   }
 
+  private describePendingRequests(): Array<Record<string, unknown>> {
+    const now = Date.now();
+    return Array.from(this.pendingRequests.entries()).map(([requestId, request]) =>
+      Object.assign(
+        {
+          requestId,
+          type: request.type,
+          ageMs: Math.max(0, now - request.startedAt),
+        },
+        request.summary,
+      ),
+    );
+  }
+
+  private getStderrTail(): string {
+    return truncateStart(this.stderrTail.trim(), STDERR_TAIL_MAX_CHARS);
+  }
+
   private rejectAllPending(error: Error): void {
     for (const [requestId, pending] of this.pendingRequests) {
       clearTimeout(pending.timeout);
@@ -344,7 +552,27 @@ export class LocalSpeechWorkerClient {
     if (!emitter) {
       return;
     }
-    emitter.emit("error", error instanceof Error ? error : new Error(String(error)));
+    this.emitErrorIfObserved(
+      sessionId,
+      emitter,
+      error instanceof Error ? error : new Error(String(error)),
+    );
+  }
+
+  private emitErrorIfObserved(
+    sessionId: string,
+    emitter: EventEmitter,
+    error: Error,
+    workerPid: number | null = this.workerPid,
+  ): void {
+    if (emitter.listenerCount("error") > 0) {
+      emitter.emit("error", error);
+      return;
+    }
+    this.logger.warn(
+      { err: error, workerPid, sessionId },
+      "Local speech worker session error had no listener",
+    );
   }
 
   private scheduleIdleShutdownIfReady(): void {